Synthesis of Building Blocks Containing Glycosyl Moieties by Using Triazinylammonium Sulfonates

Beata Kolesińska ,  Kamil Rożniakowski ,  Małgorzata Legun ,  Grażyna Relich ,  Zbigniew J. Kamiński 

Technical University of Łódź, Institute of Organic Chemistry (PŁ), Żeromskiego 116, Łódź 90-924, Poland

Abstract

Posttranslational modifications are covalent processing events that change the properties of a protein by the addition of a modifying group to one or more amino acids [1]. Growing evidences indicate that N-glucosylation is a posttranslational modication (PTM) that may play a fundamental role in a large number of biological events [2]. The most well-known modifying groups in eukaryotic proteins are glycans. Protein glycans are classified into two groups: N-linked glycans attached to asparagine (Asn) residues and O-linked glycans attached to Ser or Thr residues. Currently, the synthesis of building blocks containing glycosyl moieties, linked to the carboxyl function of aspartic acid by an amide bond, typically requires glycosylamines and efficient coupling reagents. In our previous studies [3], we examined triazine-based coupling reagent in synthesis of N-glycosylated-Asp derivative. A comparative study of the coupling reaction between glucosamine and aspartic acid was performed using DMT/NMM/BF4, CDMT, HATU, TBTU, and BOP.

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Herein, we present the studies on screening of family of N-triazinylammonium sulfonates in synthesis of building blocks containing glycosyl moieties.

Acknowledgement: This work was supported by the Grant donated by the Technical University of Łódź.

[1] (a) Ling, R.; Yoshida, M.; Mariano, P. S., J. Org. Chem. 1996, 61, 4439; (b) Doyle, H. A.; Mamula, M. J., Trends Immunol. 2001, 22, 443.
[2] Tzur,Y.; Markovich, A.; Lichtenstein, R.G., J. Proteome Res. 2008, 7, 1188–1198.
[3] Paolini, I.; Nuti, F.; Pozo-Carrero, M.; Barbetti, F.; Kolesinska, B.; Kaminski, Z.J.; Chelli, M.; Papini, A.M., Tetrahedron. Lett. 2007, 48(16) 2901-2904.

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Presentation: Poster at VI Multidyscyplinarna Konferencja Nauki o Leku, by Beata Kolesińska
See On-line Journal of VI Multidyscyplinarna Konferencja Nauki o Leku

Submitted: 2008-03-15 09:22
Revised:   2009-06-07 00:48
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